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• W1994692320 abstract "first_page settings Order Article Reprints Font Type: Arial Georgia Verdana Font Size: Aa Aa Aa Line Spacing:    Column Width:    Background: Open AccessShort Note 3-Hydroxy-4-[(phenylimino)methyl]phenyl Myristate by Sie-Tiong Ha 1,*, Siew-Teng Ong 1, Yee-Ting Chong 2 and Guan-Yeow Yeap 3 1 Department of Chemical Science, Faculty of Science, Universiti Tunku Abdul Rahman, Jln Universiti, Bandar Barat, 31900 Kampar, Perak, Malaysia 2 Department of Science & Engineering, Centre for Foundation Studies, Universiti Tunku Abdul Rahman, Building PE, No. 1 Jalan 13/4, 46200 Petaling Jaya, Selangor, Malaysia 3 Liquid Crystal Research Laboratory, School of Chemical Sciences, Universiti Sains Malaysia, Minden 11800 Minden, Penang, Malaysia * Author to whom correspondence should be addressed. Molbank 2009, 2009(4), M632; https://doi.org/10.3390/M632 Received: 26 August 2009 / Accepted: 13 October 2009 / Published: 14 October 2009 Download Download PDF Download PDF with Cover Download XML Download Epub Download Supplementary Material Browse Figures Versions Notes Abstract: A new Schiff base ester 3-hydroxy-4-[(phenylimino)methyl]phenyl myristate was synthesized and its IR, 1H NMR, 13C NMR and MS spectroscopic data are presented. Keywords: 3-hydroxy-4-[(phenylimino)methyl]phenyl myristate; Schiff base; alkyl chain Graphical Abstract Schiff bases have received a considerable amount of attention from many researchers owing to their importance in exhibiting thermochromism and photochromism [1,2,3,4]. Aromatic Schiff bases possessing long alkyl chain have received much attention due to their possibility to exhibit liquid crystalline properties such as smectic and nematic phases [5,6,7,8,9]. Synthesis4-Formyl-3-hydroxyphenyl tetradecanoate was previously prepared via Steglich esterification [10]. In a round-bottom flask, a mixture of the 4-formyl-3-hydroxyphenyl tetradecanoate (1.74 g, 5.0 mmol), aniline (0.47 g, 5.0 mmol) and absolute ethanol (50 mL) was refluxed with stirring for three hours. The reaction mixture was filtered and the solvent removed from the filtrate by evaporation. Recrystallization from absolute ethanol gave the title compound as yellow solid (1.14 g, 54%).Melting point: 103.4 oC.MS(EI): M+ (m/z) = 423 (4) [M]+, 213 (100).IR (KBr, cm-1): 3435 (O-H), 2952, 2917, 2848 (C-H aliphatic); 1754 (C=O ester); 1629 (C=N); 1594, 1499 (C=C aromatic).1H NMR (400 MHz, CDCl3): δ/ppm 0.90 (t, 3H, J = 6.9 Hz, CH3), 1.30-1.46 {m, 20H, CH3(CH2)10-}, 1.75 (q, 2H, J = 7.5 Hz, -CH2CH2COO-), 2.57 (t, 2H, J = 7.5 Hz, -CH2COO-), 6.71 (dd, 1H, J = 2.2, 8.4 Hz, Ar-H), 6.79 (d, 1H, J = 2.2 Hz, Ar-H), 7.28 (m, 3H, Ar-H), 7.39 (d, 1H, J = 8.4 Hz, Ar-H), 7.42 (m, 2H, Ar-H), 8.62 (s, 1H, CH=N), 13.60 (s, 1H, OH).13C NMR (100 MHz, CDCl3): δ/ppm 172.1 (COO), 162.2 (CH=N), 163.0, 154.9, 148.6, 133.5, 129.8, 127.4, 121.6, 117.5, 113.3, 110.9 (aromatic carbons), 34.86 (-CH2COO-), 25.30 (-CH2CH2COO-), 32.34, 30.10, 30.07, 30.02, 29.88, 29.78, 29.67, 29.50, 23.11 (CH3(CH2)14-), 14.54 (CH3).Elemental analysis: Calculated for C27H37NO3 C, 76.56%, H, 8.80%, N, 3.31%; Found: C, 76.45%, H, 8.87%, N, 3.44%. Supplementary materialsSupplementary File 1Supplementary File 2Supplementary File 3AcknowledgementsThe main author (S.T. Ha) would like to thank Universiti Tunku Abdul Rahman for the financial support and research facilities.References and NotesHadjoudis, E.; Vittorakis, M.; Moustakali-Mavridis, I. Photochromism and thermochromism of schiff bases in the solid state and in rigid glasses. Tetrahedron 1987, 43, 1345–1360. [Google Scholar]Hadjoudis, E.; Rontoyianni, A.; Ambroziak, K.; Dziembowska, T.; Mavridis, I.M. Photochromism and thermochromism of solid trans-N,N'-bis(salicylidene)-1,2-cyclohexanediamines and trans-N,N'-bis-(2-hydroxynaphylidene)-1,2-cyclohexanediamine. J. Photochem. Photobiol. A: Chem. 2004, 162, 521–530. [Google Scholar] [CrossRef]Oshima, A.; Momotake, A.; Arai, T. Photochromism, thermochromism, and solvatochromism of naphthalene-based analogues of salicylideneaniline in solution. J. Photochem. Photobiol. A: Chem. 2004, 162, 473–479. [Google Scholar]Yeap, G.Y.; Ha, S.T.; Ishizawa, N.; Suda, K.; Boey, P.L.; Mahmood, W.A.K. Synthesis, crystal structure and spectroscopic study of para substituted 2-hydroxy-3-methoxybenzalideneanilines. J. Mol. Struct. 2003, 658, 87–99. [Google Scholar] [CrossRef]Ha, S.T.; Ong, L.K.; Wong, J.P.W.; Yeap, G.Y.; Lin, H.C.; Ong, S.T.; Koh, T.M. Mesogenic Schiff's base ether with dimethylamino end group. Phase Transitions 2009, 82, 387–397. [Google Scholar] [CrossRef]Ha, S.T.; Ong, L.K.; Ong, S.T.; Yeap, G.Y.; Wong, J.P.W.; Koh, T.M.; Lin, H.C. Synthesis and mesomorphic properties of new Schiff base esters with different alkyl chains. Chin. Chem. Lett. 2009, 20, 767–770. [Google Scholar] [CrossRef]Ha, S.T.; Koh, T.M.; Ong, S.T.; Beh, J.K.; Ong, L.K. Synthesis of a new liquid crystal, 3-hydroxy-4-{[(6-methoxy-1,3-benzothiazol-2-yl)imino]methyl}phenyl palmitate. Molbank 2009, 2009, M608. [Google Scholar] [CrossRef]Ha, S.T.; Ong, L.K.; Win, Y.F.; Koh, T.M. 4-[(Pyridin-3-ylmethylene)amino]phenyltetradecanoate. Molbank 2009, 2009, M585. [Google Scholar] [CrossRef]Ha, S.T.; Ong, L.K.; Win, Y.F.; Koh, T.M. 4-[(Pyridin-3-ylmethylene)amino]phenylhexadecanoate. Molbank 2009, 2009, M584. [Google Scholar] [CrossRef]Ha, S.T.; Ong, S.T.; Chong, Y.T.; Yeap, G.Y. 4-{[(3-Chlorophenyl)imino]methyl}-3-hydroxyphenyl myristate. Molbank 2009, 2009, M629. [Google Scholar] [CrossRef] © 2009 by the authors; licensee Molecular Diversity Preservation International, Basel, Switzerland. This article is an open-access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/). Share and Cite MDPI and ACS Style Ha, S.-T.; Ong, S.-T.; Chong, Y.-T.; Yeap, G.-Y. 3-Hydroxy-4-[(phenylimino)methyl]phenyl Myristate. Molbank 2009, 2009, M632. https://doi.org/10.3390/M632 AMA Style Ha S-T, Ong S-T, Chong Y-T, Yeap G-Y. 3-Hydroxy-4-[(phenylimino)methyl]phenyl Myristate. Molbank. 2009; 2009(4):M632. https://doi.org/10.3390/M632 Chicago/Turabian Style Ha, Sie-Tiong, Siew-Teng Ong, Yee-Ting Chong, and Guan-Yeow Yeap. 2009. 3-Hydroxy-4-[(phenylimino)methyl]phenyl Myristate Molbank 2009, no. 4: M632. https://doi.org/10.3390/M632 Find Other Styles Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here. Article Metrics No No Article Access Statistics For more information on the journal statistics, click here. Multiple requests from the same IP address are counted as one view." @default.
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